Diastereocontrol by trialkylaluminums in the synthesis of tetrahydrofuransvia radical cyclization

Authors
Ericsson, C Engman, L
Citation
C. Ericsson et L. Engman, Diastereocontrol by trialkylaluminums in the synthesis of tetrahydrofuransvia radical cyclization, ORG LETT, 3(22), 2001, pp. 3459-3462
Citations number
34
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
22
Year of publication
2001
Pages
3459 - 3462
Database
ISI
SICI code
1523-7060(20011101)3:22<3459:DBTITS>2.0.ZU;2-T
Abstract
[GRAPHICS] The influence of various Lewis acids in the radical cyclization of beta -al lyloxyalkyl phenyl selenides was investigated. Whereas the unperturbed cycl ization afforded trans-2,4-disubstituted tetrahydrofurans as the major prod ucts (cis/trans approximate to 1/4.5), cyclization in the presence of trial kylaluminums (3 equiv) afforded predominantly (cis/trans approximate to 7/1 ) the corresponding cis-isomers.